Browse Promos + Events

15 ways to experience Winter Park and Maitland

It's absurd to try and capture all of Winter Park and Maitland in the space of a couple of pages, or to define it as a "neighborhood" – both are vibrant cities with neighborhoods of their own. So we'll just try to hit some of the new highlights and old favorites of this leafy, genteel region, home to Rollins College, the Park Avenue shopping district, a historic African American enclave, a charming network of canals and lakes, and some world-class museums.

Beautiful and sophisticated, the lakefront setting is as much of a draw as the culinary excellence of this Longwood spot. They've been in business for 37 years, and just this spring OpenTable ranked Enzo's one of the 100 most romantic restaurants in America.

This Maitland outpost of the MetroWest original offers an identical menu, so you can gorge on their wide selection of hefty burgers (including such delicacies as the cronut burger with half-pound of meat and maple-pepper bacon, or the "Teak Challenge" – a two-pounder with 27 slices of cheese, 24 slices of bacon) closer to home.

Luxe patisserie offers a gorgeous line of cakes, cookies, doughnuts and specialty pastries to satisfy the sweetest of tooths. Coffee from Onyx Coffee Labs (with whom they have an exclusive partnership) makes a perfect pairing, be it drip, pour-over, nitro cold brew or espresso.

One of the most authentic diners in the area has amazingly low prices in a time-warp setting: Get a Philly cheese steak with sliced sirloin and provolone and a root beer float for less than 10 bucks while marveling at the glass and aluminum capsule surrounding you.

Farmhouse sits next door to the original
Foxtail in Winter Park, offering not just overflow seating but a wine bar, cocktails on tap, fresh juice, local pastries, an experimental coffee menu, and "the world's largest coffee siphon bar."

Winter Park's boutique hotel also functions as an art gallery, hosting oft-changing selections from Rollins College's Alfond Collection of Contemporary Art. Catch a cocktail or a cup of tea in the lobby and soak up some culture.